publication . Article . 2008

Synthesis of spiroacetals using functionalised titanium carbenoids

Main, C.A.; Rahman, S.S.; Hartley, R.C.;
Open Access
  • Published: 04 Aug 2008 Journal: Tetrahedron Letters, volume 49, pages 4,771-4,774 (issn: 0040-4039, Copyright policy)
  • Publisher: Elsevier BV
  • Country: India
Abstract
Alkylidenation of lactones with functionalised titanium carbenoid reagents (Schrock carbenes) followed by acid-induced cyclisation of the resulting enol ethers constitutes a new method for the preparation of [4.4], [4.5] and [5.5] spiroacetals (1,6-dioxaspiro[4.4]nonanes, 1,6-dioxaspiro[4.5]decanes and 1,7-dioxaspiro[5.5]undecanes, respectively, sometimes termed 5,5-, 5,6- and 6,6-spiroketals). The titanium carbenoids are easily generated from readily available thioacetals.
Subjects
free text keywords: Organic Chemistry, Biochemistry, Drug Discovery, Titanium, chemistry.chemical_element, chemistry, Lactone, chemistry.chemical_classification, Carbenoid, Thioacetal, Enol, chemistry.chemical_compound, Reagent, QD
Related Organizations
26 references, page 1 of 2

1. Reviews: (a) Mead, K. T.; Brewer, B. N. Curr. Org. Chem. 2003, 7, 227-256. (b) Aho, J. E.; Pihko, P. M.; Rissa, T. K. Chem. Rev. 2005, 105, 4406-4440. (c) Perron, F.; Albizati, K. F. Chem. Rev. 1989, 89, 1617-1661.

2. Recent examples include: (a) Keaton, K. A.; Phillips, A. J. Org. Lett. 2007, 9, 2717- 2719. (b) Tsang, K. Y.; Brimble, M. A. Tetrahedron 2007, 63, 6015-6034. (c) Lu, C.- D.; Zakarian, A. Org. Lett. 2007, 9, 3161-3163. (c) Velluci, D.; Rychnovsky, S. D. Org. Lett. 2007, 9, 711-714. (e) Denmark, S. E.; Regens, C. S.; Kobayashi, T. J. Am. Chem. Soc. 2007, 129, 2774-2776. (f) Phillips, S. T.; Shair, M. D. J. Am. Chem. Soc. 2007, 129, 6589-6598. (g) Lowe, J. T.; Wrona, I. E.; Panek, J. S. Org. Lett. 2007, 9, 327-330.

3. Hayes, P.; Maignan, C. Synthesis 1999, 783-786.

4. Tietze, L. F.; Schneider, G.; Wölfling, J.; Fecher, A.; Nöbel, T.; Peterson, S.; Schuberth, I.; Wulff, C. Chem. Eur. J. 2000, 6, 3755-3760.

5. Zhou, G.; Zheng, D.; Da, S.; Xie, Z.; Li, Y. Tetrahedron Lett. 2006, 47, 3349-3352.

6. Cuzzupe, A. N.; Hutton, C. A.; Lilly, M. J.; Mann, R. K.; McRae, K. J.; Zammit, S. C.; Rizzacasa, M. A. J. Org. Chem. 2001, 66, 2382-2393.

7. Ireland, R. E.; Thaisrivongs, S.; Dussault, P. H. J. Am. Chem. Soc. 1988, 110, 5768- 5779.

8. Chang, C.-F.; Yang, W.-B.; Chang, C.-C.; Lin, C.-H. Tetrahedron Lett. 2002, 43, 6515-6519.

9. Paterson, D. E.; Griffin, F. K.; Alcaraz, M.-L.; Taylor, R. J. K. Eur. J. Org. Chem. 2002, 1323-1336.

10. Ousset, J. B.; Mioskowski, C.; Yang, Y.-L.; Falck, J. R. Tetrahedron Lett. 1984, 25, 5903-5906.

11. Godoy, J.; Ley, S. V.; Lygo, B. J. Chem. Soc., Chem. Commun. 1984, 1381-1382.

12. Wang, C.; Forsyth, C. J. Org. Lett. 2006, 8, 2997-3000.

13. Evans, D. A.; Rajapakse, H. A.; Stenkamp, D. Angew. Chem. Int. Ed. 2002, 41, 4569-4573.

14. Yang, W.-B.; Yang, Y.-Y.; Gu, Y.-F., Wang, S.-H.; Chang, C.-C.; Lin, C.-H. J. Org. Chem. 2002, 67, 3773-3782.

15. Tebbe, F. N.; Parshall, G. W.; Reddy, G. S. J. Am. Chem. Soc. 1978, 100, 3611- 3613.

26 references, page 1 of 2
Powered by OpenAIRE Research Graph
Any information missing or wrong?Report an Issue